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EP1636651B8 - Low-viscous, radiation curable formulation, particularly for the stereolithographical production of earpieces - Google Patents

Low-viscous, radiation curable formulation, particularly for the stereolithographical production of earpieces Download PDF

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Publication number
EP1636651B8
EP1636651B8 EP04738713A EP04738713A EP1636651B8 EP 1636651 B8 EP1636651 B8 EP 1636651B8 EP 04738713 A EP04738713 A EP 04738713A EP 04738713 A EP04738713 A EP 04738713A EP 1636651 B8 EP1636651 B8 EP 1636651B8
Authority
EP
European Patent Office
Prior art keywords
weight
viscosity
viscous
radiation curable
low
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP04738713A
Other languages
German (de)
French (fr)
Other versions
EP1636651A1 (en
EP1636651B1 (en
Inventor
Martin Klare
Reiner Altmann
Michael Kutschinski
Georgia Meissner
Thomas Veit
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dreve Otoplastik GmbH
Original Assignee
Dreve Otoplastik GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dreve Otoplastik GmbH filed Critical Dreve Otoplastik GmbH
Publication of EP1636651A1 publication Critical patent/EP1636651A1/en
Publication of EP1636651B1 publication Critical patent/EP1636651B1/en
Application granted granted Critical
Publication of EP1636651B8 publication Critical patent/EP1636651B8/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B29WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29CSHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C64/00Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
    • B29C64/10Processes of additive manufacturing
    • B29C64/106Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
    • B29C64/124Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
    • B29C64/129Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask
    • B29C64/135Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask the energy source being concentrated, e.g. scanning lasers or focused light sources
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B33ADDITIVE MANUFACTURING TECHNOLOGY
    • B33YADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
    • B33Y70/00Materials specially adapted for additive manufacturing
    • B33Y70/10Composites of different types of material, e.g. mixtures of ceramics and polymers or mixtures of metals and biomaterials
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0037Production of three-dimensional images
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/114Initiator containing
    • Y10S430/118Initiator containing with inhibitor or stabilizer

Landscapes

  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Mechanical Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Ceramic Engineering (AREA)
  • Civil Engineering (AREA)
  • Composite Materials (AREA)
  • Structural Engineering (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)
  • Materials For Medical Uses (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Dental Preparations (AREA)

Abstract

The invention relates to a biocompatible, low-viscous, radiation curable formulation, particularly for use in stereolithography, for use in medical technology, in particular, for producing earpieces, containing: a) 55-95% by weight of a monomeric or oligomeric dimethacrylate based on bisphenol A or bisphenol F; b) 0-20% by weight of a urethane methacrylate having a functionality of n<4 and a viscosity<15 Pa s; c) 2-15% by weight of a monomeric aliphatic or cycloaliphatic dimethacrylate having a viscosity<5 Pa s; d) 0-15% by weight of a monofunctional methacrylate having a viscosity<3 Pa s; e) 0.5-6% by weight of a photoinitiator or a combination of a number of photoinitiators whose absorption is located within the wavelength range of the laser beam used; f) 0.0001-2% by weight of the inhibitor 2,2,6,6-tetramethylpiperidin-1-yloxy (free radical), also in conjunction with known inhibitors; g) 0-40% by weight of fillers; h) 0-5% by weight of coloring pigments; i) 0-5% by weight of remaining additives such as UV stabilizers or spreading additives, whereby the proportions of constituents a) to h) total 100% by weight.
EP04738713A 2003-06-23 2004-06-17 Low-viscous, radiation curable formulation, particularly for the stereolithographical production of earpieces Expired - Lifetime EP1636651B8 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10328302A DE10328302A1 (en) 2003-06-23 2003-06-23 Low-viscosity, radiation-curable formulation, in particular for stereolithography, for use in medical technology, in particular for the production of ear pieces
PCT/DE2004/001262 WO2005001570A1 (en) 2003-06-23 2004-06-17 Low-viscous, radiation curable formulation, particularly for the stereolithographical production of earpieces

Publications (3)

Publication Number Publication Date
EP1636651A1 EP1636651A1 (en) 2006-03-22
EP1636651B1 EP1636651B1 (en) 2009-10-28
EP1636651B8 true EP1636651B8 (en) 2010-02-17

Family

ID=33546628

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04738713A Expired - Lifetime EP1636651B8 (en) 2003-06-23 2004-06-17 Low-viscous, radiation curable formulation, particularly for the stereolithographical production of earpieces

Country Status (9)

Country Link
US (1) US7232646B2 (en)
EP (1) EP1636651B8 (en)
JP (1) JP4251368B2 (en)
CN (1) CN1813220B (en)
AT (1) ATE447200T1 (en)
AU (1) AU2004252589B2 (en)
CA (1) CA2530069C (en)
DE (2) DE10328302A1 (en)
WO (1) WO2005001570A1 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004050868A1 (en) * 2004-10-18 2006-04-20 Dreve Otoplastik Gmbh Low-viscosity, radiation-curable formulation for the production of ear molds
DE102005050186A1 (en) * 2005-10-18 2007-04-19 Dreve Otoplastik Gmbh Low viscosity, radiation-hardenable composition for antimicrobial medical products, especially adaptive ear pieces, is based on e.g. (meth)acrylates, glass or silver antimicrobials and photoinitiators
US7354870B2 (en) * 2005-11-14 2008-04-08 National Research Council Of Canada Process for chemical etching of parts fabricated by stereolithography
DE102007017195A1 (en) * 2007-04-12 2008-10-16 Dreve Otoplastik Gmbh Biocompatible, radiation-curing formulation for the generative production of medical-technical products, in particular earmolds and dental moldings, by means of image projection systems
DE102007041489A1 (en) 2007-08-31 2009-03-05 Deltamed Gmbh Flexible medical-technical molded body and method for its production
EP2445028A1 (en) 2010-10-25 2012-04-25 Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO Opto-electric device and method of manufacturing an opto-electric device
EP2445029A1 (en) * 2010-10-25 2012-04-25 Nederlandse Organisatie voor toegepast -natuurwetenschappelijk onderzoek TNO Multilayered protective layer, organic opto-electric device and method of manufacturing the same
US10357435B2 (en) * 2012-12-18 2019-07-23 Dentca, Inc. Photo-curable resin compositions and method of using the same in three-dimensional printing for manufacturing artificial teeth and denture base
DK2986654T3 (en) * 2013-04-18 2020-05-25 Dentca Inc Light-curing resin compositions and methods for using them for three-dimensional printing to make artificial teeth and denture base
EP3234035B1 (en) * 2014-12-18 2021-06-02 BASF Coatings GmbH Radiation curable composition comprising hydrophilic nanoparticles
CN112313577B (en) 2018-04-20 2024-07-09 斯特拉塔西斯公司 Radiation curable compositions for additive manufacturing
US20230365830A1 (en) * 2020-10-08 2023-11-16 Dic Corporation Resin composition for stereolithography
CA3197362A1 (en) 2020-11-30 2022-06-02 Dinesh Kumar BASKER Radiation curable resin

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0425441B1 (en) * 1989-10-27 1995-12-27 Ciba-Geigy Ag Photosensitive mixture
DE4009602A1 (en) * 1990-03-26 1991-10-02 Ivoclar Ag POLYMERIZABLE DENTAL MATERIAL
GB9504995D0 (en) * 1995-03-11 1995-04-26 Zeneca Ltd Compositions
DE59701299D1 (en) * 1996-07-29 2000-04-27 Ciba Sc Holding Ag Liquid, radiation-curable composition, especially for stereolithography
US5969000A (en) * 1997-01-17 1999-10-19 Jeneric Pentron Incorporated Dental resin materials
US6569602B1 (en) * 1998-10-05 2003-05-27 E. I. Du Pont De Nemours And Company Ionization radiation imageable photopolymer compositions
DE10108261B4 (en) * 2001-02-21 2006-07-20 Ivoclar Vivadent Ag Polymerizable composition with particulate composite based filler
US6660208B2 (en) * 2001-03-30 2003-12-09 3D Systems, Inc. Detoxification of solid freeform fabrication materials
JP2002302523A (en) * 2001-04-04 2002-10-18 Rion Co Ltd Stereolithography resin
EP1456307B1 (en) * 2001-10-03 2011-12-07 3D Systems, Inc. Phase change support material composition
GB0212062D0 (en) * 2002-05-24 2002-07-03 Vantico Ag Jetable compositions
US6989225B2 (en) * 2002-07-18 2006-01-24 3D Systems, Inc. Stereolithographic resins with high temperature and high impact resistance

Also Published As

Publication number Publication date
DE502004010300D1 (en) 2009-12-10
EP1636651A1 (en) 2006-03-22
CN1813220A (en) 2006-08-02
ATE447200T1 (en) 2009-11-15
DE10328302A1 (en) 2005-01-27
CA2530069C (en) 2009-12-22
US20060264526A1 (en) 2006-11-23
EP1636651B1 (en) 2009-10-28
AU2004252589B2 (en) 2007-03-22
US7232646B2 (en) 2007-06-19
WO2005001570A1 (en) 2005-01-06
AU2004252589A1 (en) 2005-01-06
JP2007500759A (en) 2007-01-18
JP4251368B2 (en) 2009-04-08
CN1813220B (en) 2010-11-03
CA2530069A1 (en) 2005-01-06

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